The final rule, “The Rule of Patience” tells me if you are building a company, not a product or feature (see “The Black Tee Rule”), it will take you seven-plus years from beginning to an exit. So settle in for the long game, because it’s going to be a while before you see that big payout people love to brag about.

When I first joined the ranks of venture capital, one of the LPs in the fund came into my office saying he wanted to “meet the $25 million man.” Clueless, I asked him what that meant. He explained to me the average new general partner loses $25 million before maybe figuring it out, thus the $25 million man.

As an investor, I have been good and perhaps lucky, but I have still lost my $25 million. For every loss, I have a “lessons learned” list. Whenever I think I know anything I read the list to remind me that I don’t. I have made enough mistakes to be able to group lessons learned into categories such as mistakes made in diligence (for example, check to see who is related to each other despite having different last names) to patience, lack thereof, or even too much.

For the record, I didn’t do this alone. My co-investors were right beside me swinging away from the black tees, going after those really difficult, yet high potential problems. For LPs, like the one who came into my office, this is simple math. For every one dollar they give me, if I give them more than three back, I keep my job. If I give them less than three, chances are it will cost them $25 million to train my replacement. Essentially, with an investment of X you are looking for a return of Y, where X/Y is greater than three.

Here are five free lessons learned under the heading “Patience, lack thereof or too much” that take the form of a few choice metaphors.

You can control your burn, but not the market.

Venture investors will tell you to skate to where the puck will be. I did a deal where we “knew” the puck was going to be free at the top of the crease without a goalie in the net. We just didn’t know exactly when. We lost patience and told the team to get revenue from a side product. Unfortunately, by the time we figured out that net was wide open another competitor got there first. They won the first large deployment not because they had a better solution (we did) but they kept playing hockey. We got our product to market four months behind them and took second place. Two thirds of the value accrued to the winner.

I lost $8 million on this one; it still hurts. The team was tantalizingly close to solving very difficult technical problems in material sciences. The investors kept adding both cash and hope, but eventually seven years to exit became 10. The syndicate fractured with some funds running out of reserves, other funds pushing for liquidity. Employees were fully vested. They either left or ask for re-ups further diluting patient investors.

Moral of the story. Ensure that between the team, board and advisors you have the technical depth to know if you are in research or development. You burn a boatload of cash if you think you are in development but are really in research so figure it out early, plan for the outcome and know how to get there.

Does Gen 1 = Gen 2?

I lost another pile on a company that focused on first adopters, delivered faster than their competitors, got into volume production first, hit double digit millions in revenue and raised a another significant chunk of capital at a nice up round to build generation two of the product.

Unfortunately, the skills to develop second generation solutions were very different from those needed for the first hit they created. I suspected we had the wrong team in place for this leg of the journey but failed to take action until it was too late. We fired the CEO eventually but, by the time the replacement troops arrived, we were almost out of ammo.

Note to self:

1. Firing a CEO costs at least $1 million

2. Once you suspect you have an issue, be much more impatient—the wrong CEO costs you much more than one million dollars.